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How NFL Insiders Are Building Wealth Through Short-Term Rentals on Florida’s 30A Coast

Rental Property Owner & Real Estate Investor Podcast

Release Date: 09/15/2025

Conference Announcement: Midwest Real Estate Investor Conference April 27–28, 2026 show art Conference Announcement: Midwest Real Estate Investor Conference April 27–28, 2026

Rental Property Owner & Real Estate Investor Podcast

The Midwest Real Estate Investor Conference (MREIC) is back April 27–28, 2026 at DeVos Place in Grand Rapids, Michigan, and this year’s theme is Thrive. This quick special announcement features Erika Farley, Executive Director of the Rental Property Owners Association of Michigan (RPOAM), breaking down what’s new, who it’s for, and why you should lock in your ticket now. () You’ll hear how the 2026 agenda is built around systems, real-world strategy, and operating resilience, including major focus on AI integration and a grounded economic outlook for 2026 that investors can...

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The Truth About Subject-To, Seller Finance, and the Risks Most Investors Miss with Caleb Christopher show art The Truth About Subject-To, Seller Finance, and the Risks Most Investors Miss with Caleb Christopher

Rental Property Owner & Real Estate Investor Podcast

Creative financing opens amazing doors for real estate investors—but it can also destroy deals when done wrong. In this episode, Caleb Christopher, founder of Creative TC, breaks down how to use Subject-To and Seller-Financing strategies safely, legally, and ethically. Caleb shares real-world stories from the trenches—like taking over a mortgage where the sellers actually paid him—and explains what to watch out for when banks threaten the due-on-sale clause. You’ll learn: What creative financing really means (and when you should—or shouldn’t—use it) How to protect...

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How Real Estate Investors Can Use AI Right Now: Chatbots, Automation & Smarter Decisions with Clay Lehman show art How Real Estate Investors Can Use AI Right Now: Chatbots, Automation & Smarter Decisions with Clay Lehman

Rental Property Owner & Real Estate Investor Podcast

Artificial intelligence is transforming every corner of real estate—from how we analyze deals to how we manage tenants, leads, and operations. But most investors still don’t know where to start. In this episode, Brian Hamrick talks with Clay Lehman, a longtime investor, property-management expert, and AI educator who helps entrepreneurs and agents use today’s tools to save time, make better decisions, and grow their business. You’ll learn: The fundamentals vs. hype of AI in real estate investing How to use Google Gemini, Notebook LM, and Claude for research, analysis, and...

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What Every New Developer Needs to Know Before the First Shovel Hits the Ground with Steve Achram and Peter Skornia show art What Every New Developer Needs to Know Before the First Shovel Hits the Ground with Steve Achram and Peter Skornia

Rental Property Owner & Real Estate Investor Podcast

Every successful real estate development starts long before the first shovel hits the ground. From concept and capital stack to design, construction, and operations—understanding the process is key to building with purpose. In this episode, Steve Achram and Peter Skornia of Cella Building Company in Grand Rapids, Michigan, share a step-by-step guide to sustainable development and walk us through their Wealthy & Sheldon project—an example of how thoughtful design, solid financial modeling, and community collaboration can turn a vision into a high-performing building. We cover: What...

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Property Management Secrets: Reducing Delinquencies, Tenant Psychology & Turning Around Underperforming Properties with Craig Marquardo show art Property Management Secrets: Reducing Delinquencies, Tenant Psychology & Turning Around Underperforming Properties with Craig Marquardo

Rental Property Owner & Real Estate Investor Podcast

Underperforming properties are where the biggest money is made—if you know how to fix them. That’s where expert property management comes in. In this episode, Brian speaks with Craig Marquardo, VP of Multifamily at VCS Property Management, who has over 20 years of experience cleaning up operations, boosting tenant retention, and maximizing NOI. Craig pulls back the curtain on how property managers really operate and what every owner needs to know to protect their investment. You’ll learn: Tenant Psychology: How residents think about rent increases and what keeps them paying on time. ...

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Creative Foreclosure Investing: How to Profit from Overages and Distressed Deals with Bob Diamond show art Creative Foreclosure Investing: How to Profit from Overages and Distressed Deals with Bob Diamond

Rental Property Owner & Real Estate Investor Podcast

Negotiation, deal structure, and legal traps—these can make or break a real estate investor. Few people understand this better than Bob Diamond, a seasoned real estate attorney, investor, and developer featured on Fox, NBC, NPR, and TLC’s Flip That House. With 30 years of legal and investing experience, Bob has personally negotiated more than $100 million in real estate transactions and authored three books on real estate investing. In this episode, he shares powerful strategies investors can use today to thrive in a shifting market, including: Overages 101: How to claim surplus funds...

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How to Get Tenants to Pay Rent on Time and Build Credit with Lily Liu show art How to Get Tenants to Pay Rent on Time and Build Credit with Lily Liu

Rental Property Owner & Real Estate Investor Podcast

One of the biggest challenges for rental property owners is ensuring residents pay on time—and keeping them motivated to stay. What if you could turn rent into a win-win, boosting your cash flow while helping tenants improve their credit and earn rewards? In this episode, Brian talks with Lily Liu, founder and CEO of Pinata, a fast-growing platform that transforms rent payments into financial progress. Lily shares how Pinata helps: Renters build credit by reporting on-time payments to all three bureaus Property owners increase on-time payments by 20% or more Landlords and managers...

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Building Wealth with Sustainable Materials: How Climate Innovation is Reshaping Real Estate with Josh Dorfman show art Building Wealth with Sustainable Materials: How Climate Innovation is Reshaping Real Estate with Josh Dorfman

Rental Property Owner & Real Estate Investor Podcast

For investors, developers, and property owners, the future of real estate isn’t just about location—it’s about building smarter, cheaper, and more sustainably. In this episode, Brian Hamrick sits down with Josh Dorfman, climate entrepreneur, media personality, and co-founder of Plantd, a carbon-negative building materials company recognized by Fast Company as one of the most innovative in the world. Josh has spent his career at the intersection of business and sustainability. You may know him as the creator of The Lazy Environmentalist (Sundance Channel, Sirius XM, and two books). Today,...

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Why Every Real Estate Investor Needs Title Insurance: Protecting Your Deals from Liens, Fraud, and Hidden Risks with Dru Wischhover show art Why Every Real Estate Investor Needs Title Insurance: Protecting Your Deals from Liens, Fraud, and Hidden Risks with Dru Wischhover

Rental Property Owner & Real Estate Investor Podcast

Most real estate investors love hunting for great deals—but few think about the unglamorous step that can make or break a transaction: title insurance. In this episode, Brian Hamrick sits down with Dru Wischhover, Founder and CEO of Inspired Title Group, who brings over 20 years of experience in navigating the hidden risks of property ownership. Dru has seen everything from divorce decrees gone wrong to fraudulent deeds and wire scams—and he explains why title insurance is one of the most important safeguards you can have as an investor. You’ll discover: The difference between...

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From Duplex to $10 Million Portfolio: Bob Biggins’ Path to 500 Doors show art From Duplex to $10 Million Portfolio: Bob Biggins’ Path to 500 Doors

Rental Property Owner & Real Estate Investor Podcast

What does it take to grow from a single duplex to managing 85 units worth nearly $10 million—and then set your sights on 500 doors? In this episode, Brian Hamrick talks with Bob Biggins, a Michigan-based investor, licensed realtor, and YouTube creator who has been in real estate for nearly 30 years. Starting with a house-hack duplex in the 1990s, Bob slowly built his portfolio while working a corporate job. Today, after exiting that career, he’s fully focused on multifamily investing and scaling up. You’ll learn: How Bob used education and persistence to build a solid foundation in...

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More Episodes

What do NFL players, luxury beach homes, and high-stakes real estate deals have in common? Brooke Kromer.

In this episode, we dive into the world of high net worth investing in Florida’s exclusive 30A market, where multimillion-dollar short-term rentals are helping athletes, coaches, and savvy investors grow and preserve wealth.

Brooke Kromer—realtor, investor, and daughter of longtime NFL coach Aaron Kromer—shares how she uses her insider knowledge and lifelong NFL connections to guide players and entrepreneurs into strategic real estate investments along the Gulf Coast. We talk about:

  • Why 30A is booming for short-term rental investing

  • How Brooke walks first-time buyers and NFL stars through deals worth $1M–$25M

  • Real numbers: what it costs to buy, hold, and earn rental income in this luxury market

  • How athletes navigate pressure, family dynamics, and financial decisions

  • The tax advantages and bonus depreciation strategies being used right now

  • Why Brooke left a successful career in sports broadcasting to take control of her future through real estate

  • What makes the 30A lifestyle a magnet for high performers and tech entrepreneurs

Whether you're an investor, sports fan, or curious about how the ultra-wealthy think about real estate, this is a behind-the-scenes look you won’t want to miss.

Follow Brooke Kromer:

https:// www.facebook.com/kromercollective

https:// www.instagram.com/brookekromer/

https:// www.youtube.com/@BrookeKromerRealEstate

brooke.kromer@compass.com

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Today’s episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area.

https://www.livegreenlocal.com

And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and Medicare benefits.

https://www.rcbassociatesllc.com

Topics:
30A Florida real estate, short-term rentals, NFL investors, high net worth real estate, tax strategies for Airbnb, luxury vacation homes, real estate for athletes, Rosemary Beach investing, strategic wealth building.